When in 1783 it became clear that a band of American rebels had succeeded in their insurrection against King George, Robert Pagan and 443 of his neighbors in Castine, Maine, did the only thing loyal subjects of the Crown could do: they dismantled their houses and pubs, board by board and nail by nail, piled them onto schooners, and sailed for the northern Crown colonies. There, at the confluence of the St. Croix River and Passamaquoddy Bay, just a coin’s throw across the Maritime border of what is now Maine, the Penobscot Loyalists shook the dust of revolution from their heels and secured a piece of the Empire. Financed by the royal treasury and carefully laid out in advance by George III’s deputy surveyor general of Nova Scotia, St. Andrews would become a paragon of royal benevolence and Loyalist industry.

Two centuries later St. Andrews is still a paragon, a town of redolent English gardens, gleaming white churches, and classic houses abiding in the shade of hoary elms and chestnuts. Though born as a Loyalist Canaan and nurtured as a tumultuous mercantile hub in the age of sail, St. Andrews emerged from the nineteenth century not as a commercial prodigy but as a resort, a Maritime haunt for the famous, the near famous, and the indisputably rich from both sides of the border. The thread that binds all three eras, and the enduring appeal of this community on the cusp of the Old World and the New Republic, is a varied architecture with a distinctive vernacular tang, set in a region cut whole from the quarry of North America—one of the last areas on the Eastern seaboard still bearing some semblance to what John Cabot found in 1497.

The Penobscot Loyalists set ashore beside the site of what is now Market Wharf, which hooks like a great fish barb far into the bay from the heart of Water Street, the town’s main byway. Come by sea or come by land, Water Street is a surprise; few places in North America have better preserved themselves against the caustic flow of time. Across from the wharf your eye catches the 1881 Shiretown Inn, originally the Kennedy Hotel and one of the two oldest summer hotels in Canada. A young Franklin Delano Roosevelt stayed here on an overnight yachting jaunt from the family cottage on nearby Campobello Island. To your immediate left is the plain brick custom-house, which once employed the father of Oliver Goldsmith, namesake and grandnephew of the eighteenth-century AngloIrish poet. Young Goldsmith published the first book of poetry by a native Canadian, its title work a paean to his Loyalist birthplace, St. Andrews. He called it The Rising Village, an allusion to his uncle’s 1770 masterpiece, The Deserted Village. Now walk to Water Street and glance left. A block or so down is the Dunn-McQuoid house, St. Andrews’s first two-story building, disassembled in New York and reerected here in 1784. Its rafters still bear the crudely etched numbers used to reconstruct it. A block to the right of the wharf is but one of a number of exemplary Cape Cod cottages, this one built in 1808 by Fenwick Bell, a sea captain.

You don’t have to walk far. Nearly every building is distinguished by some curious bit of history, some period detail: a weathered gray tin or cedarshingle roof; a mix of gingerbread bargeboard. Geraniums bloom on white porches, blue lobelia trails from window boxes, and hand-carved signs invite you to sample the shopkeepers’ wares: fine imported and domestic woolens, Wedgwood sold at the company’s first dealership in North America, or Inuit wildlife sculpture coaxed from stone the color of leaden Arctic skies.

Now cross to King Street, which intersects Water at the mouth of the wharf. King is the spine of the residential district, intersecting first Queen Street, then, at the top of the hill, Prince of Wales. Two blocks right is Princess Royal. The Loyalists named these streets in honor of King George, Queen Charlotte, and their fifteen children. They ran out of streets, the joke went, before the royal couple ran out of offspring.

As you walk, what strikes you is the scale and dimension of the town, which conveys an implacable sense of proportion that is very much a part of the overall aesthetic of its age. Unlike the usual pioneer-town scheme—a central pasture or “common” with narrow streets sprawling outward—the king’s surveyor plotted St. Andrews into a graceful matrix of sixty perfectly square blocks, each composed of eight ample house lots of identical measure, 80 by 160 feet. The blocks were delineated by unusually broad streets. In the east and west wings of the town, he situated two “Public Reserves,” or parks, like counterbalances in a clock. A third he centered at the head of the wharf. These are no longer there. Twelve additional lots on the harbor below Water Street were assigned for commercial use.

St. Andrews’s gridiron pattern represented one of the first instances of urban planning in Canada. Here was a plan philosophically in harmony with the neoclassical world view already shaken by the American Revolution and soon to be swept away by the French Revolution and the romantic juggernaut of the nineteenth century. The surveyor’s scheme, moreover, had a practical consequence: Large house lots and wide navigable streets for vehicles conferred extraordinary protection against fire, an ever-present danger in communities composed largely of wooden structures that relied year-round on wood fuel for heating and cooking. Today over 250 of St. Andrews’s 550 buildings are more than a hundred years old, and many are two hundred or more.

Within five years the town put up six hundred buildings and had a larger population than it does today.

The Nova Scotia settlements were derided by swaggerers in the newly minted United States—“Nova Scarcity” they called the colony, referring to the early hardships incurred by the exiles, including many in St. Andrews, especially during their second winter. But in May 1784, just six months after landing, William Pagan, Robert’s brother, could boast to John Adams’s old Loyalist friend Dr. William Paine: “We have now about: Ninety Houses up, and great preparations making in every quarter … for more. Numbers of inhabitants are daily arriving and a great many others are hourly looked for.” He noted with satisfaction that “a number of valuable inhabitants … wish to emigrate here, being tired of their new Government.” Dr. Paine was among them.

For three years the king provisioned the Loyalists with the essentials—food, tools, window glass, livestock—which they transformed almost overnight into the farms, sawmills, shipbuilding shops, and wharves on which their wealth would depend. Within five years the town erected six hundred buildings and the population swelled to three thousand, larger than it is today. So inundated with refugees—more than thirty thousand in all—was the whole Fundy region that in 1784 New Brunswick, “the Loyalist Province,” was carved from Nova Scotia’s northwestern precints. Today, if you ask a New Brunswicker where his family originally hails from, he is as likely to tell you New Jersey or even Plymouth Plantation as London.

By 1803 the town was cresting on the enormous wartime profits gained by Britain’s long conflict with revolutionary France and later with Napoleon. St. Andrews was cutting four hundred thousand board feet of lumber annually and had built forty-two square-rigged commercial vessels since 1784. As many as a hundred schooners might sail on a single outgoing tide. St. Andrews was ferrying the wealth of the Empire in a mercantile triangle between New Brunswick, Britain, and the West Indies, thus realizing the province’s motto, Spem Reduxit (“Hope Restored”).

The town’s prosperity was soon reflected in the houses, churches, and public buildings that constitute the civic wealth of any community. English by choice but Yankee by heritage, the Loyalists at first built houses derivative of the colonial styles they had left behind: ground-hugging, functional Capes and modest Georgians, the architectural standards of the age in both America and Britain.

Architects were scarce at first in the Fundy region, but skilled cabinetmakers and ship carpenters abounded. Using the so-called pattern books of the era—popular manuals providing floor plans for fashionable contemporary buildings—local craftsmen melded indigenous materials and local needs into a comprehensive architectural sampler. Within the central district’s 1.5 square miles—roughly the area of Central Park in New York City—the next century in St. Andrews produced a medley of the most influential building styles of three hundred years: Palladian, Georgian, neoclassical, Greek Revival, and later the fabulous miscellany of styles included under the broad rubric of the Victorian Romantic Revival. And St. Andrews prospered mightily, well into the new century, in spite of the War of 1812, an Anglo-American conflict that Loyalists elsewhere regarded as a continuation of the Revolution. For those in the Fundy region—a people who had already made their peace at the counting table—the war was largely a nuisance brewed in Washington and London. St. Andrews built two blockhouses and a fort, but its most effective defense, and that of its U.S. neighbors, was an agreement among the border towns to simply treat the conflict as an exercise. Still standing and unscathed, St. Andrews’s remaining blockhouse is the last of twelve martial defenses on the coast. It has survived not so much the trials of war as the ravages of time; its various big guns never fired a shot in anger. In fact, the only items exchanged by the 1812 “combatants” were not bullets but contraband gypsum for plaster walls. The war merely encouraged an already lucrative commerce in smuggling; Benedict Arnold himself had run a brisk business out of nearby Campobello Island in the 1780s. Smugglers “traded on the lines,” transferring goods at the border without actually crossing it. Yankee pragmatism, recall, was a common heritage.

By 1820, after the world’s first severe industrial depression, which followed the Napoleonic Wars, legal trade too flourished. And it was in the increasing finery of their new homes that the merchant princes of St. Andrews best expressed their civic sensibilities. The simple Georgian bloomed into the neoclassical town house. (Some architectural historians use the terms neoclassical and Federalist interchangeably, though the word Federalist, for obvious reasons, never gained currency in Canada.) Like its Georgian antecedent, the neoclassical house is gracefully proportioned, but it incorporates a profusion of classical motifs: ornately detailed pediments, pilasters, and columns, decorative gable windows, and an elaborate central entry. A fine example at St. Andrews is Chestnut Hall, home of the Ross Museum.

Chestnut Hall was built about 1810 by the son of the Boston Loyalist Col. Christopher Hatch, who, like Robert Pagan, had been proscribed as a traitor and banished from Massachusetts in 1778. Little changed over the years, the house was acquired in 1938 by the American philanthropists Henry Phipps Ross and Sarah Juliette Ross, his wife, whose father was an early chief at Dun & Bradstreet. The museum is furnished with the Rosses’ extensive collection of antique furniture and decorative arts, some from China but much of it the accomplished artistry of nineteenth-century New Brunswick cabinetmakers. Because the pieces are exhibited in the context of a private home, you can’t help feeling that you’re a privileged guest in another era.

In St. Andrews, staunch Loyalists were for the most part staunch Anglicans, since membership in the Church of England was required to obtain a royal land grant. The first minister to arrive, in 1786, was the Anglican clergyman Samuel Andrews, of Connecticut. (The town had been named not for Parson Andrews but for St. André by a seventeenth-century French Jesuit.) The original Anglican church, built in 1790 but now gone, served all congregations until 1818, when the Reverend John Cassilis, a Presbyterian minister from Scotland, decided to build his own kirk, as the Scottish church is called. The project soon ran out of funds, however, inviting the sectarian scorn of the Episcopalians. One evening at a dinner party a wealthy Scottish merchant, smuggler, and rumored privateer named Christopher Scott suffered a slur about the idleness of Presbyterian saints and resolved to finance the church himself. Thus St. Andrews acquired what many regard as its architectural centerpiece: the Greenock Presbyterian Church.

In the 1850s, after sixty years of furious economic activity, St. Andrews went bust.

The Greenock builders too were guided by the pattern books, notably Asher Benjamin’s popular New England builders’ series. Hence the church combines three traditions—New England, New Brunswick, and Scottish. Its crowning glory, plunging heavenward through the tree line, is its triumphant spire, modeled on a Christopher Wren steeple in Scotland.

Entering the church’s narrow double doors, you find two long galleries, left and right, supported by solid bird’seye maple pillars. The central pulpit rises to the level of the galleries and is clasped shut by gates, symbolizing the exclusion of worldly things. Look carefully. You’ll find not a nail or metal brace in the entire edifice; the craftsmen cut and carved each member lovingly, painstakingly, from prime Honduran mahogany and local bird’s-eye maple, locking them together, like hands in prayer, with invisible bonds. The silver communion chalices, the collection boxes, the pulpit Bible, and the box pews are all original.

A few blocks north and east, you’ll find the 1791 Loyalist Burying Ground, the final resting place of many town fathers, including Robert Pagan and Thomas Wyer, who in 1777 escaped a dunking in a Massachusetts tar barrel by traveling two hundred miles in an open boat to Nova Scotia. Angus McDonald, a cousin of Flora Macdonald, Jacobite heroine and accomplice of Bonnie Prince Charles, lies here too, as do a number of sailors “in harbor here below,” hapless women lost in childbirth, and young victims of those once inscrutable and intractable poxes and fevers of childhood.

The cemetery’s most dramatic inhabitant is Charles Briscoe, who died in 1830, a wraithlike figure who had wandered the town on a great white horse and hinted that the bluest of blood ran through his veins. He claimed, moreover, to have papers to prove it, which he had buried with him with the provision that they be disinterred fifty years after his death. The documents, after half a century in the damp Maritime soil, were illegible; nevertheless, an ivory miniature bearing the image of George IV was found. From this scant evidence, an artifact set in pearls and bound with a locket of hair, some believe Briscoe to be the natural son of the regent George and Mrs. Fitzherbert, a Roman Catholic, whom he married secretly in London in 1785. The marriage was officially declared childless.

A block from the Loyalist cemetery is the 1840 Charlotte County Courthouse, the oldest Canadian courthouse in continuous use. The building is Classical Revival in style—a more ponderous version of the neoclassical—and its pediment bears Victoria’s royal coat of arms, the lion and chained unicorn. Beside the courthouse, in austere contrast, squats the granite jail, built in 1832 and closed in 1979. From here, on occasion an inmate was led to the gibbet on the courthouse green.

By the middle of the nineteenth century, after sixty years of volatile economic activity, St. Andrews went bust, its prosperity swept away by the power of steam and the decision to establish its rival, St. John, as the region’s primary railway terminus. However, St. Andrews did not languish like other Maritime boom towns in the waning age of sail; it soon flowered anew, as a playground for the rich and powerful.

St. Andrews’s gilded age was shaped by an informal nineteenth-century alliance between the nation’s political power brokers—just then forging Canada’s first independent government—and the captains of industry, particularly the principals of the Canadian Pacific Railway. Between them, they parlayed the town’s natural beauty and remarkable past into an unprecedented commodity, the Maritime summer resort. Within a generation, solid St. Andrews, the Loyalist refuge and commercial wonder, would become chic St. Andrews-by-the-Sea, the “Newport of the North.” Before long, travelers would come from as far away as St. Louis, Washington, and New York, and the floating palaces of the Vanderbilts and Morgans would idle at anchor just offshore.

Promoters soon realized that a first-class resort required a first-class hotel and a convenient way to get to it. In 1871 two events conspired to secure the success of the fledgling summer colony. The first occurred in Bangor, Maine, when President Grant drove the last spike of the Maine and St. John Railway. The new line cut the trip to St. Andrews from Boston and Montreal, which had entailed a long trip by steamer for the last leg, to less than twenty-four hours. The second event was the commissioning of the Argyll Hotel, the first resort complex on Canada’s East Coast. The depression of the 1870s delayed completion for a decade, but the Argyll finally opened on May 24, 1881, Victoria’s birthday.

The Argyll prospered under the management of the New Brunswick and Canada Railway, and in 1889 another syndicate of steamship and railroad moguls, mostly from Boston and Bangor, built St. Andrews’s present-day grand hotel, the Algonquin. Fire, which had destroyed the Argyll in 1892, ravaged the Algonquin in 1914, but it was rebuilt in a single season. Today the 187-room hotel rises above the hill on Prince of Wales like a rambling old English manor house in Tudor style, an ivy-clad edifice of whitewashed walls with dark wood trim, green-trellised verandas, bannered turrets, and a sunbleached red-slate roof. The landscaping and architecture of the Algonquin weave a spell so reminiscent of the turn of the century that you almost expect to see couples whirling to Strauss behind the trellised windows. Even the staff participates in the illusion; kilted bellboys whisk away your baggage and at dusk lower the flags, both Canadian and American, to the thrilling wheeze of bagpipes.

At dusk kilted bellboys lower the flags, both Canadian and American, to the wheeze of bagpipes.

From the beginning St. Andrews’s history had been braided with ours, and this was no less true in the resort era than in any other. Because the Algonquin was an international enterprise, representatives of both nations, including the governor general of Canada and the governor of Maine, attended its opening. Some of the Algonquin’s Boston backers took up residence in town and went on to become naturalized and distinguished Canadian citizens. Without question, however, St. Andrews’s most prominent American-born resident at this time was Sir William Van Horne, the corpulent general manager of the Canadian Pacific Railway. Lured to the CPR as much by an irresistible challenge as by the highest salary ever paid a Western railroad man—a scandalous fifteen thousand dollars a year—Van Horne was the genius behind Canada’s 1885 transcontinental railway, a vast and daunting enterprise confronting stern and variegated terrain. Ardent Canadian nationalists branded him a “Yankee Trojan horse,” but the only horse he ever gave a damn about was the iron horse. He completed the project in just four years. In 1894 Victoria raised him to the peerage, after Van Horne had twice declined the honor, and the scrappy kid from the Illinois Central’s railyards became “Sir William.”

The distinction did little to refine his Yankee earthiness. A man of prodigious appetites and childlike exuberance—“I eat all I can, I drink all I can, I smoke all I can, and I don’t give a damn for anything!” he once boomed—Van Horne brought a spark of genius and a talent for conspicuous consumption to the Grafting of Covenhoven, his Dutch-style manor house on five-hundred-acre Minister’s Island just off St. Andrews’s northern shore. Covenhoven, like a castle with a fickle moat, is accessible only twice daily, when the titan Fundy tides retreat to expose a subaquatic road to the island.

When Van Horne ran into difficulties enlarging Covenhoven, he contracted a gifted young Canadian architect, Edward Maxwell, to advise him. Maxwell would one day design Regina’s legislative buildings and Montreal’s Museum of Fine Arts. His signature style, however, was the picturesque Queen Anne Revival cottage, popularized in the United States as the Shingle Style. The antithesis of the well-proportioned Georgian, the Queen Anne home was irregular, almost eccentric, in plan, shape, color, and texture. It employed what one writer described as an “almost medieval arrangement of roofs, dormers, chimneys and gables” to suggest elegance without formality. Consonant with the fey aesthetic mood of the era, houses acquired fanciful titles—Clibrig, Les Goelands, Berwick Brae—that sounded straight out of a Sir Walter Scott novel. The apotheosis of the Queen Anne Revival house can be seen at Maxwell’s own summer retreat, Tillietudlem, opposite Minister’s Island. Others—Hillcrest, Meadow Lodge, and Rosemount—are just a leisurely walk from the Algonquin.

Today, on the Algonquin’s trellised veranda, the descendants of Loyalists and revolutionaries can share an incendiary nine o’clock sunset secure in a mutual respect for a kindred heritage. Yet St. Andrews’s mystique for Americans has always run deeper than merely an appreciation for fine architecture and natural setting, a fraternal ancestry, and a genteel past. It has to do with a warp in the fabric of Anglo-American history, a heightened appreciation for the grace, traditions, and, above all, the resilient British spirit that we south of the border, by some ineradicable instinct, long to claim as our own—a spirit composed of the same British traits of individualism and initiative that animated both the rebel cause and the Loyalists’ stolid reaction to it. More than two centuries ago at a dinner party in colonial Massachusetts given by John Adams’s Loyalist friend Dr. Paine, who eventually settled in St. Andrews, Adams rejoined a toast to “His Britannic Majesty” with an impudent toast to “His Satanic Majesty.” Mrs. Paine, unfazed, remarked that “as the gentleman has been so good to drink to the health of the King, let us by no means refuse to drink to his friend.” Perhaps even John Adams would agree it’s time to give the devil his due.